CR6086   

GtoPdb Ligand ID: 9845

Compound class: Synthetic organic
Comment: CR6086 is a potent and selective prostaglandin E2 receptor 4 (EP4) antagonist that that is being investigated for immunomodulatory potential, that may be suitable for the treatment of rheumatoid arthritis [1].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 69.64
Molecular weight 472.2
XLogP 5.23
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES O=C(C1CC2(CCN1Cc1ccc(cc1)C(F)(F)F)CC2)NC1(CC1)c1ccc(cc1)C(=O)O
Isomeric SMILES O=C([C@H]1CC2(CCN1Cc1ccc(cc1)C(F)(F)F)CC2)NC1(CC1)c1ccc(cc1)C(=O)O
InChI InChI=1S/C26H27F3N2O3/c27-26(28,29)20-5-1-17(2-6-20)16-31-14-13-24(9-10-24)15-21(31)22(32)30-25(11-12-25)19-7-3-18(4-8-19)23(33)34/h1-8,21H,9-16H2,(H,30,32)(H,33,34)/t21-/m1/s1
InChI Key CADWTPLFEZSAHM-OAQYLSRUSA-N
Bioactivity Comments
CR6086 at concentrations up to 10 μM showed no significant binding affinities for the other eicosanoid receptors and did not inhibit COX enzyme activities [1].
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
EP4 receptor Hs Antagonist Antagonist 9.3 pKd - 1
pKd 9.3 (Kd 5.4x10-10 M) [1]
EP4 receptor Rn Antagonist Antagonist 8.7 pKd - 1
pKd 8.7 (Kd 1.96x10-9 M) [1]
EP4 receptor Mm Antagonist Antagonist 8.7 pKd - 1
pKd 8.7 (Kd 2.14x10-9 M) [1]
EP4 receptor Hs Antagonist Antagonist 7.8 pKi - 1
pKi 7.8 (Ki 1.66x10-8 M) [1]